• 제목/요약/키워드: Stereocontrol

검색결과 9건 처리시간 0.027초

Total Synthesis of ($\pm$)-Homoepibatidine

  • Kim, Yong-Hyun;Won, Do-Youn;Oh, Chang-Young;Lee, Kee-Young;Jeong, Jin-Hyun;Jung, Young-Hoon;Ham, Won-Hun
    • Archives of Pharmacal Research
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    • 제22권4호
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    • pp.435-436
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    • 1999
  • Total synthesis of ($\pm$)-homoepibatidine (2), which contains the 8-azabicyclo[3.2.1] octane ring system, was achieved by using palladium-catalyzed Heck-type coupling reaction from 3.

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Enantioselective Synthesis of Cyclic Amino Alcohols: cis-1-Amino-2-indanol

  • Kim, Eun-Jin;An, Kyung-Mi;Ko, Soo Y.
    • Bulletin of the Korean Chemical Society
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    • 제27권12호
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    • pp.2019-2022
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    • 2006
  • (1S,2R)-cis-1-Amino-2-indanol has been synthesized. A unique feature of the synthesis involves securing the functionalities and the configurations of the two stereocenters on an acyclic precursor before cyclizing it into the final ring-skeleton. The strategy allows both the stereocenters to be controlled in an absolute manner.

Synthesis of Perhydroisoquinoline Ring Systems by N-Acyliminium Cyclization$^\sharp$

  • Choi, Joong-Kwon;Jung, Young-Shik;Park, No-Sang
    • Bulletin of the Korean Chemical Society
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    • 제9권3호
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    • pp.129-132
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    • 1988
  • The stereochemistry of N-acyliminium cyclizations to form decahydropyrrolo[2,1-a]isoquinolin-3(2H)-ones was studied. Particular attention was paid to the stereocontrol by an acetoxy group present on pyrrolidone ring. Two of the three new chiral centers were formed stereospecifically, and the third was controlled by elimination-hydrogenation sequence.

Approach to the Total Synthesis of Acanthoside-D

  • Ngoc, Thyen-Truong;Park, Hae-Il
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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    • pp.186.4-187
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    • 2003
  • Acanthoside-D, one of major components of Acanthopanacis Cortex, is known as a ginseng-like substance. it has been known to possess diverse biological effects. Acanthoside-D has a furofuran lignan structure and the synthesis of which poses interesting and often unsolved proplems of stereocontrol. Although a few interesting syntheses providing this natural product have been reported, an intermolecular McMurry coupling - intramolecular Mitsunobu cyclization route has not yet been explored. We report here a short and efficient synthetic pathway to the total synthesis of Acanthoside-D from aryl aldehydes and methyl acrylates via Baylis-Hillman reaction, intermolecular McMurry coupling and intramolecular Mitsunobu cyclization as key reaction.

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Diastereoselective Synthesis of Polysubstituted Pyrrolidinone as a Key Intermediate for the Anticancer Agents by Palladium(II)­Catalyzed Carboxylation

  • Choi Dong-Rack;Lee Kee-Young;Chung Yun-Sung;Joo Jae-Eun;Kim Yong-Hyun;Oh Chang-Young;Lee Yiu-Suk;Ham Won-Hun
    • Archives of Pharmacal Research
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    • 제28권2호
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    • pp.151-158
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    • 2005
  • Palladium(II)-catalyzed carboxylation of chiral olefins 6a-d has been examined under various conditions. In the weak basic condition ($K_{2}CO_3$), 7a-d were obtained in good yields. Alternatively, in the strong basic condition, pyrrolidinones 8a-d were obtained resulting in excellent yields and with high diastereoselectivity.

Stereoselective Syntheses of ($\pm$)-Epibatidine Analogues

  • Kim, Yong-Hyun;Won, Do-Youn;Oh, Chang-Young;Lee, Kee-Young;Lee, Yiu-Suk;Woo, Nam-Tae;Park, Young-Ho;Park, Hyun-Ju;Ham, Won-Hun
    • Archives of Pharmacal Research
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    • 제25권1호
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    • pp.45-48
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    • 2002
  • Stereoselective syntheses of ($\pm$)-epibatidine analogues 2, which contain the 8-azabicyclo[3.2.1]octane ring system, were achieved by using palladium-catalyzed cross-coupling reaction from 4 and the analgesic activity was tested by Mouse writhing antinociceptive assay.

Syntheses of ($\pm$)-Homoepibatidine Analogues

  • Kim, Yong-Hyun;Oh, Chang-Young;Lee, Kee-Young;Lee, Yiu-Suk;Jung, Young-Hoon;Park, Hyun-Ju;Ham, Won-Hun
    • Archives of Pharmacal Research
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    • 제25권1호
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    • pp.49-52
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    • 2002
  • Syntheses of ($\pm$)-homoepibatidine analogues (2), which contain the 8-azabicyclo [3.2.1 ]octane ring system, were achieved by using palladium-catalyzed reductive-coupling reaction from 3 and the analgesic activity was tested by Mouse writhing antinociceptive assay

Diastereoselective Synthesis of anti-1,2-Aminoalcohol by Palladium(II) Catalyzed Aza-Claisen Rearrangement

  • Yoon, Youn-Jung;Chan, Myung-Hee;Joo, Jae-Eun;Kim, Yong-Hyun;Oh, Chang-Young;Lee, Kee-Young;Lee, Yiu-Suk;Ham, Won-Hun
    • Archives of Pharmacal Research
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    • 제27권2호
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    • pp.136-142
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    • 2004
  • In this study, a highly diastereoselective synthesis of anti-1 ,2-aminoalcohol was explored starting from L-amino acids as chiral sources. The higher yield and diastereoselectivity was shown when the aza-Claisen rearranqement was performed with allylic trichloroacetimidate 6a in the presence of palldium(II) catalyst.